CAS 136470-78-5|Abacavir

Introduction：Basic information about CAS 136470-78-5|Abacavir, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Abacavir BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Synonyms

Common Name	Abacavir
CAS Number	136470-78-5	Molecular Weight	286.332
Density	1.7±0.1 g/cm3	Boiling Point	636.0±65.0 °C at 760 mmHg
Molecular Formula	C₁₄H₁₈N₆O	Melting Point	161 °C(dec.)
MSDS	/	Flash Point	338.4±34.3 °C

Names

Name	abacavir
Synonym	More Synonyms

Abacavir BiologicalActivity

Description	Abacavir is a powerful nucleoside analog reverse transcriptase inhibitor (NRTI) used to treat HIV and AIDS. IC50 value:Target: NRTI; reverse transcriptase inhibitorAbacavir is a nucleoside reverse transcriptase inhibitor marketed since 1999 for the treatment of infection with the human immunodeficiency virus type 1 (HIV). Despite its clinical efficacy, abacavir administration has been associated with serious and sometimes fatal toxic events. Abacavir has been reported to undergo bioactivation in vitro, yielding reactive species that bind covalently to human serum albumin, but the haptenation mechanism and its significance to the toxic events induced by this anti-HIV drug have yet to be elucidated. The mechanism underlying abacavir hypersensitivity syndrome is related to the change in the HLA-B5701 protein product. Abacavir binds with high specificity to the HLA-B5701 protein, changing the shape and chemistry of the antigen-binding cleft. This results in a change in immunological tolerance and the subsequent activation of abacavir-specific cytotoxic T cells, which produce a systemic reaction known as abacavir hypersensitivity syndrome.
Related Catalog	Signaling Pathways >>Anti-infection >>HIVSignaling Pathways >>Anti-infection >>Reverse TranscriptaseResearch Areas >>Infection
References	[1]. Charneira C, et al. Reactive aldehyde metabolites from the anti-HIV drug abacavir: amino acid adducts as possible factors in abacavir toxicity. Chem Res Toxicol. 2011 Dec 19;24(12):2129-41. [2]. Hervey PS, et al. Abacavir: a review of its clinical potential in patients with HIV infection. Drugs. 2000 Aug;60(2):447-79.

Description

Abacavir is a powerful nucleoside analog reverse transcriptase inhibitor (NRTI) used to treat HIV and AIDS. IC50 value:Target: NRTI; reverse transcriptase inhibitorAbacavir is a nucleoside reverse transcriptase inhibitor marketed since 1999 for the treatment of infection with the human immunodeficiency virus type 1 (HIV). Despite its clinical efficacy, abacavir administration has been associated with serious and sometimes fatal toxic events. Abacavir has been reported to undergo bioactivation in vitro, yielding reactive species that bind covalently to human serum albumin, but the haptenation mechanism and its significance to the toxic events induced by this anti-HIV drug have yet to be elucidated. The mechanism underlying abacavir hypersensitivity syndrome is related to the change in the HLA-B*5701 protein product. Abacavir binds with high specificity to the HLA-B*5701 protein, changing the shape and chemistry of the antigen-binding cleft. This results in a change in immunological tolerance and the subsequent activation of abacavir-specific cytotoxic T cells, which produce a systemic reaction known as abacavir hypersensitivity syndrome.

Related Catalog

Signaling Pathways >>Anti-infection >>HIVSignaling Pathways >>Anti-infection >>Reverse TranscriptaseResearch Areas >>Infection

References

[1]. Charneira C, et al. Reactive aldehyde metabolites from the anti-HIV drug abacavir: amino acid adducts as possible factors in abacavir toxicity. Chem Res Toxicol. 2011 Dec 19;24(12):2129-41.

[2]. Hervey PS, et al. Abacavir: a review of its clinical potential in patients with HIV infection. Drugs. 2000 Aug;60(2):447-79.

Chemical & Physical Properties

Density	1.7±0.1 g/cm3
Boiling Point	636.0±65.0 °C at 760 mmHg
Melting Point	161 °C(dec.)
Molecular Formula	C₁₄H₁₈N₆O
Molecular Weight	286.332
Flash Point	338.4±34.3 °C
Exact Mass	286.154205
PSA	101.88000
LogP	0.72
Vapour Pressure	0.0±2.0 mmHg at 25°C
Index of Refraction	1.864
InChIKey	MCGSCOLBFJQGHM-SCZZXKLOSA-N
SMILES	Nc1nc(NC2CC2)c2ncn(C3C=CC(CO)C3)c2n1
Storage condition	0-6°C

Safety Information

Hazard Codes	T,N
Risk Phrases	R21:Harmful in contact with skin. R23/25:Toxic by inhalation and if swallowed . R43:May cause sensitization by skin contact. R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
Safety Phrases	S36/37-S45-S60-S61
RIDADR	UN 2810
RTECS	TE3850000
Packaging Group	III
Hazard Class	6.1(b)

Synonyms

MFCD00903850

(1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol

(1S,cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol

2-Cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-, (1S,4R)-

Abacavir

2-Cyclopentene-1-methanol, 4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-, (1S,4R)-

2-Cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-, (1S-cis)-

{(1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopenten-1-yl}methanol

{(1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol

{(4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol

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